1) Ann love path: You meet her at the bar at the beginning of the game. Choose to be nice and understanding to her, but guide her during sexual experimentation. It leads to loving sex at the end of 0.5.
2) Ann corruption path: You meet her at the bar too. Guide her during experimentation, and also be aggressive and demanding every time you can. One day Ann will ask you to go to the cinema, where you will meet Alex in real life. For the threesome: Remember to call Vanessa and tell her that you are visiting Ann before the last scene. Vanessa will be there but just to spice things up, you will not fuck her.
3) Vanessa's friend path. You meet her at the bar instead of Ann. Flirt with her whenever you can. Don't blackmail her when she sucks off the bartender. At the bar, don't ask Joey to drink the spiked shot that Vanessa prepared for Ann. If you told her that a sextape would be a good present for Joey, they will invite you over to record it for them. You will get naked but not participate. You can still have fun with Ann if you chose her during bottle game, kissed her in the bar...
4) Vanessa's blackmail paths.
You need to meet Vanessa at the bar, go back there the next day and see the sexual photo on the bartender's phone. Later you will call Vanessa and meet her at the cafe where she works. Blackmail her. Two paths here:
A) Sex with Vanessa:
If you don't tell Joey in the gym about your blackmailing Vanessa, you'll still be friends and they will still invite you to shoot the sextape. However, at the bar you first need to trick him into drinking the shot with the drug that Vanessa prepared for Ann. This way, during the sextape shooting Vanessa will suck your cock and later you will have the option to fuck her when Joey passes out.
B) Joey becomes your rival:
If you tell Joey about how you blackmailed Vanessa, he will be furious and become your enemy. Vanessa will hate you for blackmailing her and then breaking your promise. Joey's birthday party at the bar is called off, but Vanessa still takes Ann out for a drink (or two, or...). Ann will call you and ask you to join them; there, you need to tell Ann you don't like her(*). After coming back home alone, a stranger (ahem) will text you using Vanessa's phone and asking you to help her since she looks very drunk. You go back to the bar and have 2 options: drink a shot from her belly button (Joey arrives and gets really pissed off) or take her home. The next day you'll go back to her home to give her back her phone. No sex scene for you at the end of this path.
C) This is a variation of path B. You meet an "interesting" girl named Merry:
You need to follow B and get to the bar with the girls. At the bar you need to encourage Ann to drink a shot. Then let her talk and reject her when she tries to kiss you. When Vanessa asks you to go with her you need to go to Ann instead. Choose any of the three options, she will go to the toilet anyway, leaving you alone with Chris. You have to choose to be nice to him and accept his deal to exchange chicks. The following day he calls you and introduces you to Merry. WARNING: It leads to non-explicit NTR involving Ann right after the bar scene. Besides, in this path Chris demands that you share any girl around you so I'm quite positive our "roommate" will get involved at some point.
(*) By rejecting Ann you will push her into a relationship with Chris, the bartender. You will see them together on Insta and she will still receive sexual lessons from Vanessa, but this time you'll not be the lucky one. So bear this in mind.